Triphenylphosphine → 4-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone

HRID 2203020Notes

Reaction equation

HRID 2203020 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1.[Br:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28]O)[N:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCCOC)=O)=NC(OCCOC)=O>C1COCC1.CCOC(C)=O>[Br:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28][O:18][C:15]2[CH:16]=[CH:17][N:12]([C:9]3[CH:10]=[CH:11][C:6]4[N:7]([C:20]([CH3:21])=[C:4]([CH:1]5[CH2:3][CH2:2]5)[N:5]=4)[CH:8]=3)[C:13](=[O:19])[CH:14]=2)[N:27]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 2763211(2-Bromo-1,3-thiazol-4-yl)methanolHCID 533844152-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamateHCID 896902811-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1213862404-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinoneYield 47.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (239 mg), (2-bromothiazol-4-yl)methanol (330 mg) and triphenylphosphine (669 mg) in THF (5 ml) was added bis(2-methoxyethyl) azodicarboxylate (597 mg), and the mixture was stirred at room temperature for 3 h. The mixture was diluted with EtOAc, washed with water and brine successively, concentrated in vacuo, and purified by silica gel column chromatography (EtOAc/MeOH) to give the title compound (185 mg) as a white solid.

Workup

  1. washwashed with water and brine successively
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel column chromatography (EtOAc/MeOH)

Sources & evidence

ORD record
ord-f07cf830a60242708f797f2ea6fbaf60
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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