2-Bromo-1,3-thiazole-5-carboxamide → HCID 68328459, compound

HRID 634293Notes

Reaction equation

HRID 634293 reaction equation
[C:1]([NH:5][C:6]1[O:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](S(C2C=CC(C)=CC=2)(=O)=O)[CH:15]=[C:14]3B2OC(C)(C)C(C)(C)O2)=[N:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:40]1[S:41][C:42]([C:45]([NH2:47])=[O:46])=[CH:43][N:44]=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>[C:1]([NH:5][C:6]1[O:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[C:40]2[S:41][C:42]([C:45]([NH2:47])=[O:46])=[CH:43][N:44]=2)=[N:9][N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 203286042-Bromo-1,3-thiazole-5-carboxamideHCID 534244962-Chloro-1,3-thiazole-5-carboxamideHCID 68328226HCID 68328226, compound

Product 1

HCID 68328459HCID 68328459, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound (49 mg, 52% yield) as a yellow crystalline solid was prepared similar to that described in Example 275, using N-tert-butyl-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 (131 mg, 0.244 mmol), 106 mg of the 1:1 mixture of 2-bromothiazole-5-carboxamide and 2-chlorothiazole-5-carboxamide, and Pd(PPh3)4 (Strem Chemicals, 14 mg) as the starting materials and reagent. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.21 (1H, br.), 8.63 (1H, s), 8.38 (s, 1H), 8.28 (1H, s), 8.14 (1H, br.), 7.75 (1H, d, J=8.80 Hz), 7.66 (2H, m), 7.53 (1H, br.), 1.40 (9H, s). MS (ESI, pos. ion) m/z: 383.0 (M+H)+.

Sources & evidence

ORD record
ord-637752d3babc4e1994b8f5842f38d0cc
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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