Potassium Carbonate → HCID 67235968, compound

HRID 447170Notes

Reaction equation

Br[C:2]1[CH:33]=[CH:32][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][N:12]([C:15](=[O:31])[C@@H:16]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:17][C:18]4[S:19][CH:20]=[CH:21][CH:22]=4)[CH2:11][CH2:10]3)[S:8][C:4]=2[CH:3]=1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.[Cl-].[Na+].O>[O:31]=[C:15]([N:12]1[CH2:11][CH2:10][N:9]([C:7]2[S:8][C:4]3[CH:3]=[C:2]([C:39]4[CH:40]=[CH:41][C:36]([C:35]([F:46])([F:45])[F:34])=[CH:37][CH:38]=4)[CH:33]=[CH:32][C:5]=3[N:6]=2)[CH2:14][CH2:13]1)[C@@H:16]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH2:17][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 95 °C

Procedure

(S)-tert-Butyl 1-(4-(6-bromobenzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (80 mg), 4-(trifluoromethyl)phenylboronic acid (33 mg), palladium tetrakistriphenylphosphine (8 mg), and potassium carbonate (54 mg) were combined in 1,4-dioxane (5 mL) and water (1 mL). The resulting mixture was heated to 95° C. overnight, then diluted with brine, extracted with DCM, concentrated, and chromatographed (100% DCM) to yield (S)-tert-butyl 1-oxo-3-(thiophen-2-yl)-1-(4-(6-(4-(trifluoromethyl)phenyl)benzo[d]thiazol-2-yl)piperazin-1-yl)propan-2-ylcarbamate as a colorless oil (96 mg).

Workup

extractionextracted with DCM
concentrationconcentrated
customchromatographed (100% DCM)

Sources & evidence

ORD record: ord-8beb75d0c01347b5b94d62b05a032394
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481547B2

Reaction notes

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