Water → 1,1-dimethylethyl {4-[2-(1H-pyrrolo[2,3-b]pyridin-4-yl)-3-thienyl]phenyl}carbamate

HRID 28937

Reaction equation

Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]2[N:13](S(C3C=CC(C)=CC=3)(=O)=O)[CH:14]=[CH:15][C:8]=12.[C:26]([NH:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].O.[OH-].[Ba+2].[OH-]>COCCOC.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>[NH:13]1[C:9]2=[N:10][CH:11]=[CH:12][C:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[C:37]3[CH:36]=[CH:35][C:34]([NH:33][C:26](=[O:27])[O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[CH:39][CH:38]=3)=[C:8]2[CH:15]=[CH:14]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-(3-bromo-2-thienyl)-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridine (5.3 mmol) in 40 mL of 1,2-dimethoxyethane was added 4-(N-Boc-amino)phenyl boronic acid (13.8 mmol), tetrakis(triphenylphosphine)palladium(0), (0.17 mmol), water (16 mL) and barium hydroxide (21.2 mmol). The reaction was heated at 80° C. for 36 h. The 1,2-dimethoxyethane was evaporated and the residue taken up in ethyl acetate and washed with water (50 mL). The crude product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to give the title compound (40%). ESMS [M+H]+: 392.2

Workup

customThe 1,2-dimethoxyethane was evaporated
washwashed with water (50 mL)
customThe crude product was purified by silica gel chromatography (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-86e5bffe89514f43856b684c8f1e506d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07419988B2

Linked notes

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