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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → Tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate

HRID 1177572
Notes
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Reaction equation

HRID 1177572 reaction equation
CC(C)([O-])C.[Na+].I[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[C:18]([C:23]2([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:25][CH2:24]2)[N:17]=3)=[CH:10][CH:9]=1.Cl.[NH2:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:26]1([C:23]2([C:18]3[N:17]=[C:16]4[S:15][C:14]([C:11]5[CH:12]=[CH:13][C:8]([NH:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:9][CH:10]=5)=[N:22][C:21]4=[CH:20][CH:19]=3)[CH2:25][CH2:24]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 23676156Sodium t-butoxideHCID 671116852-(4-Iodophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

Product 1

HCID 67111678Tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Sodium tert-butoxide (21 mg, 0.213 mmol) was added to a mixture of 2-(4-iodophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (40.4 mg, 0.089 mmol), tert-butyl 3-aminopropanoate hydrochloride (19 mg, 0.107 mmol), Pd2(dba)3 (2.0 mg, 2.2 μmol), and Xantphos (5.1 mg, 8.9 μmol) in toluene (1.0 mL), and the resulting mixutre was heated under argon at 80° C. for 15 h. The reaction mixture was then cooled to 25° C. and concentrated onto silica gel. Chromatographic purificaiton (silica gel, 0-50% EtOAc/hexanes) furnished tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate as a yellow oil. MS (ESI) m/z: Calculated: 471.2; Observed: 472.1 (M++1).

Workup

  1. temperatureThe reaction mixture was then cooled to 25° C.
  2. concentrationconcentrated onto silica gel

Sources & evidence

ORD record
ord-52e6a33dc9f74fed85bd4fd23aca82cf
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842685B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes