Sodium Carbonate → HCID 58204239, compound

HRID 1849047Notes

Reaction equation

[NH2:1][CH2:2][C@@H:3]([OH:5])[CH3:4].Br[C:7]1[CH:30]=[CH:29][C:10]2[C:11]3[N:12]=[C:13]([C:19]4[N:20]([CH2:24][C:25]([F:28])([F:27])[F:26])[N:21]=[CH:22][N:23]=4)[S:14][C:15]=3[CH2:16][CH2:17][O:18][C:9]=2[CH:8]=1.C1(P(C2C=CC=CC=2)C2C3[O:50][C:49]4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[OH:5][C@@H:3]([CH3:4])[CH2:2][NH:1][C:49]([C:7]1[CH:30]=[CH:29][C:10]2[C:11]3[N:12]=[C:13]([C:19]4[N:20]([CH2:24][C:25]([F:28])([F:27])[F:26])[N:21]=[CH:22][N:23]=4)[S:14][C:15]=3[CH2:16][CH2:17][O:18][C:9]=2[CH:8]=1)=[O:50]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (S)-1-Amino-propan-2-ol in degassed toluene (2.32 mL) under nitrogen atmosphere was added 8-Bromo-2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene, Pd(OAc)2, 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene and sodium carbonate. The mixture was purged with carbon monoxide and heated to 90° C. under a carbon monoxide balloon for 24 hours. The reaction was diluted with ethyl acetate, filtered through celite, and purified by reverse-phase HPLC to give 107. MS(ESI+) 454.0

Workup

customThe mixture was purged with carbon monoxide
additionThe reaction was diluted with ethyl acetate
filtrationfiltered through celite
custompurified by reverse-phase HPLC

Sources & evidence

ORD record: ord-0619c59699044d7bb8c13414f5c2a2eb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952043B2

Reaction notes

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