2-Bromo-1,3-thiazole-5-carboxamide → HCID 68328817, compound

HRID 634292Notes

Reaction equation

HRID 634292 reaction equation
[CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15](S(C2C=CC(C)=CC=2)(=O)=O)[CH:14]=[C:13]3B2OC(C)(C)C(C)(C)O2)=[N:8][N:9]=1)([CH3:3])[CH3:2].Br[C:39]1[S:40][C:41]([C:44]([NH2:46])=[O:45])=[CH:42][N:43]=1.ClC1SC(C(N)=O)=CN=1>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>[CH3:3][CH:1]([NH:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[C:13]3[C:39]2[S:40][C:41]([C:44]([NH2:46])=[O:45])=[CH:42][N:43]=2)=[N:8][N:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 203286042-Bromo-1,3-thiazole-5-carboxamideHCID 534244962-Chloro-1,3-thiazole-5-carboxamideHCID 68328163HCID 68328163, compound

Product 1

HCID 68328817HCID 68328817, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound (55 mg, 40% yield) as a yellow crystalline solid was prepared according to compound 275, using N-isopropyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (150 mg, 0.287 mmol), 125 mg of the 1:1 mixture of 2-bromothiazole-5-carboxamide and 2-chlorothiazole-5-carboxamide, and Pd(PPh3)4 (Strem Chemicals, 17 mg) as the starting materials and reagent. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.19 (1H, d, J=2.3 Hz), 8.66 (1H, s), 8.38 (1H, s), 8.31 (1H, d, J=2.7 Hz), 8.13 (1H, br.), 8.01 (1H, d, J=6.8 Hz), 7.77 (1H, dd, J=8.5, 1.7 Hz), 7.64 (1H, d, J=8.6 Hz), 7.56 (1H, br.), 3.77 (1H, m), 1.25 (6H, d, J=6.5 Hz). MS (ESI, pos. ion) m/z: 369.0 (M+H)+.

Sources & evidence

ORD record
ord-8c31846b508b420bb638d47d8d8cfb30
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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