Dimethylformamide → 5-(1-Methylindol-2-yl)-1,3-thiazole-2-ylamine

HRID 1524240Notes

Reaction equation

HRID 1524240 reaction equation
Br[C:2]1[S:6][C:5](C(N)=O)=[N:4][CH:3]=1.[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC.[Cl-].[Na+].O.C[N:41](C=O)C>O>[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[C:12]1[C:2]1[S:6][C:5]([NH2:41])=[N:4][CH:3]=1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 62657Potassium Phosphate, TribasicHCID 224972475-Bromo-1,3-thiazole-2-carboxamideHCID 22733820(1-Methyl-1H-indol-2-yl)boronic acidHCID 131718255Brine ethyl acetate

Product 1

HCID 871477225-(1-Methylindol-2-yl)-1,3-thiazole-2-ylamineYield 18.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (tert-butoxy)-N-(5-bromo(1,3-thiazol-2-yl)carboxamide (52, 140 mg, 0.5 mmol), 1-methylindol-2-yl boronic acid (88 mg, 0.5 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane complex (1:1) (40 mg) and potassium phosphate (106 mg) in 2 ml DMF and 0.5 ml water was heated under Ar in microwave reactor at 150° C. for 30 min. The reaction mixture was worked up with EA/brine. Org. phase was concentrated and then subjected to silica gel flash column purification (0-100% B, A: hexane; B: EA) to give 21 mg 5-(1-methylindol-2-yl)-1,3-thiazole-2-ylamine (53) as brown solid (yield: 18.3%; purity>90%).

Workup

  1. concentrationphase was concentrated
  2. customsubjected to silica gel flash column purification (0-100% B

Sources & evidence

ORD record
ord-0f0f385892fc41d09dbb5f50aec88504
Source dataset
uspto-grants-2015_07
Patent number
US09079891B2

Reaction notes

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