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Cesium carbonate → 6-(6-Bromo-imidazo[1,2-a]pyridin-8-ylamino)-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester

HRID 402951
Notes
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Reaction equation

HRID 402951 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:15]=[N:16][C:17]([NH2:20])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21][C:22]1[CH:23]=[C:24](I)[C:25]2[N:26]([CH:28]=[CH:29][N:30]=2)[CH:27]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:24]3[C:25]4[N:26]([CH:28]=[CH:29][N:30]=4)[CH:27]=[C:22]([Br:21])[CH:23]=3)=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 49839963tert-Butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylateHCID 712991706-Bromo-8-iodoimidazo[1,2-a]pyridine

Product 1

HCID 866868476-(6-Bromo-imidazo[1,2-a]pyridin-8-ylamino)-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester
Yield 81%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-amino-3′,4′,5′,6′-tetrahydro-2′H-[3,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (971 mg, 3.0063 mmol), 6-bromo-8-iodo-imidazo[1,2-a]pyridine (1 g, 3.6075 mmol), Pd2(dba)3 (138 mg, 0.1503 mmol), XantPhos (174 mg, 0.3006 mmol), and Cs2CO3 (2 g, 6.0126 mmol) were combined in dioxane (20 mL) and the solution was stirred at 90° C. under N2 atmosphere for 5 h at which point the TLC showed little starting material remained. The solution was poured onto water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated. Purification by column chromatography on silica gel (DCM: MeOH, 60:1 eluent) afforded the desired product as yellow solid (1.15 g, 81%). 1H NMR (300 MHz, CDCl3): δ 8.44 (d, J=1.5 Hz, 1H), 8.20 (d, J=2.1 Hz, 1H), 7.92 (s, 1H), 7.84 (d, J=1.5 Hz, 1H), 7.49 (s, 2H), 7.42 (dd, J=8.4, 2.4 Hz, 1H), 6.84 (d, J=8.4 Hz, 1H), 4.27-4.23 (m, 2H), 2.85-2.77 (m, 2H), 2.68-2.58 (m, 1H), 1.84-1.79 (m, 2H), 1.67-1.57 (m, 2H), 1.48 (s, 9H).

Workup

  1. additionThe solution was poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (DCM: MeOH, 60:1 eluent)

Sources & evidence

ORD record
ord-240c25810e10408a80dfa4b05b3c89f2
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08742098B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes