1,3-Dibromobenzene → (S)-tert-butyl 2-(3-(3-hydroxypyrrolidin-1-yl)phenyl)-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate

HRID 2089427Notes

Reaction equation

HRID 2089427 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[CH:3]=1.[NH:9]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10]1.Br[C:16]1[S:17][C:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[C:19]([C:21](=[O:29])[NH:22][C:23]2[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=2)[N:20]=1>>[OH:14][C@H:11]1[CH2:12][CH2:13][N:9]([C:4]2[CH:3]=[C:2]([C:16]3[S:17][C:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])=[C:19]([C:21](=[O:29])[NH:22][C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[N:20]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:10]1

Participants

4

Reactant 3

HCID 79271,3-DibromobenzeneHCID 2733874(3S)-pyrrolidin-3-olHCID 67438038tert-butyl 2-bromo-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate

Product 1

HCID 67438298(S)-tert-butyl 2-(3-(3-hydroxypyrrolidin-1-yl)phenyl)-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamateYield 40%

Procedure

Following the procedure for Example 273 starting with 1,3-dibromobenzene and (S)-pyrrolidin-3-ol and tert-butyl 2-bromo-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate gave (S)-tert-butyl 2-(3-(3-hydroxypyrrolidin-1-yl)phenyl)-4-(1-methyl-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate as a yellow solid (110 mg, 40%). LCMS (ES+) m/z 485 (M+1)

Sources & evidence

ORD record
ord-94d64947d5b54707bf6a9b4cb5b680eb
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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