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Water → tert-butyl 5-bromo-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate

HRID 634155
Notes
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Reaction equation

HRID 634155 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2I.CN(C=O)C.C([Sn](CCCC)(CCCC)[C:29]1[N:34]=[C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)[CH:32]=[CH:31][CH:30]=1)CCC.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[C:5]2[C:29]1[CH:30]=[CH:31][CH:32]=[C:33]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)[N:34]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 17749978tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylateHCID 185257394-(6-(Tributylstannyl)pyridin-2-yl)morpholine

Product 1

HCID 68328180tert-butyl 5-bromo-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylateYield 53.13%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of Pd(PPh3)4 (255.0 mg, 220.6 μmol), tert-butyl 5-bromo-3-iodo-1H-indole-1-carboxylate (1000 mg, 2369 μmol) and CuI (546.2 mg, 2868 μmol) was added DMF (12 mL) followed by 4-(6-(tributylstannyl)pyridin-2-yl)morpholine (1000 mg, 2206 μmol). The mixture was heated at 100° C. for 20 min. After cooled to RT, the reaction was added H2O (5 mL) and DCM (5 mL). The organic layer was separated. The aqueous layer was extracted with DCM (10 mL×2). The organic layers were combined, dried with sodium sulfate, filtered and evaporated to dryness. The brown crude oil was purified with silica gel chromatography (eluting with 100% DCM) to give tert-butyl 5-bromo-3-(6-morpholinopyridin-2-yl)-1H-indole-1-carboxylate (537.3 mg, 53.13%) as a white solid. MS (ESI, pos. ion) m/z: 458 (M+1). 1H NMR (400 MHz, DMSO-d6) ppm 1.66 (s, 9H), 3.50-3.62 (m, 4H), 3.74-3.83 (m, 4H), 6.80 (d, J=8.4 Hz, 1H), 7.33 (d, J=7.4 Hz, 1H), 7.54 (dd, J=8.9, 2.1 Hz, 1H), 7.64 (dd, J=8.4, 7.6 Hz, 1H), 8.06 (d, J=9.0 Hz, 1H), 8.29 (s, 1H), 8.68 (d, J=2.2 Hz, 1H)

Workup

  1. temperatureAfter cooled to RT
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with DCM (10 mL×2)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe brown crude oil was purified with silica gel chromatography (eluting with 100% DCM)

Sources & evidence

ORD record
ord-87ffd03e504a411b8a5a149f10ec4c31
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321756B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes