Potassium Carbonate → Ethyl 2-[5-[[(1,1-dimethylethoxy)carbonyl]amino]-4,5,6,7-tetrahydro-1H-indazol-1-yl]-4-methyl-5-thiazolecarboxylate

HRID 43938Notes

Reaction equation

HRID 43938 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][CH:6]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5][C:4]=2[CH:3]=[N:2]1.Br[C:19]1[S:20][C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]([CH3:24])[N:23]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[C:13]([O:12][C:11]([NH:10][CH:6]1[CH2:7][CH2:8][C:9]2[N:1]([C:19]3[S:20][C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]([CH3:24])[N:23]=3)[N:2]=[CH:3][C:4]=2[CH2:5]1)=[O:17])([CH3:14])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 67316380(4,5,6,7-Tetrahydro-1H-indazol-5-yl)-carbamic acid tert-butyl ester

Product 1

HCID 67548772Ethyl 2-[5-[[(1,1-dimethylethoxy)carbonyl]amino]-4,5,6,7-tetrahydro-1H-indazol-1-yl]-4-methyl-5-thiazolecarboxylateYield 23%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

The same operation as in Example (223a) was performed using tert-butyl 4,5,6,7-tetrahydroindazol-5-ylcarbamate obtained in Example (242b) (246 mg, 1.04 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (519 mg, 2.07 mmol), copper (I) iodide (40 mg, 0.21 mmol), proline (48 mg, 0.42 mmol) and potassium carbonate (431 mg, 3.12 mmol), to obtain 96 mg of ethyl 2-{5-[(tert-butoxycarbonyl)amino]-4,5,6,7-tetrahydro-1H-indazol-1-yl}-4-methyl-1,3-thiazole-5-carboxylate as a pale yellow solid (23%).

Sources & evidence

ORD record
ord-913a9bf0e36d43a0b4ef000abed42515
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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