Tris(1,1-dimethylethyl)phosphine → 2-Methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide

HRID 2354512Notes

Reaction equation

HRID 2354512 reaction equation
C(C1C=C(C(C)C(C2C=CC(Cl)=CC=2)([NH:13][C:14](=[O:29])[C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][N:20]=2)([CH3:17])[CH3:16])C)C=C(F)C=1)#N.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[F:28][C:25]([F:26])([F:27])[C:22]1[CH:23]=[CH:24][C:19]([O:18][C:15]([CH3:16])([CH3:17])[C:14]([NH2:13])=[O:29])=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 68656889HCID 68656889, compound

Product 1

HCID 578519072-Methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide

Reagents, catalysts & solvents 1

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalyst

Procedure

N-[2-(3-Cyano-5-fluorophenyl)-4-hydroxyphenyl)-1-methylpropyl]-2-(5-trifluoromethyl-2-pyridyloxy)-2-methylpropanamide was prepared from N-[2-(3-cyano-5-fluorophenyl)-(4-chlorophenyl)-1-methylpropyl]-2-(5-trifluoromethyl-2-pyridyloxy)-2-methylpropanamide (Step A, slower eluting isomer) following the procedure described in Reference Example 8, Step B using tris(dibenzylideneacetone) dipalladium and tri(tert-butyl)phosphine as the catalyst. 1H NMR (500 MHz, CD3OD): δ 8.27 (d, 1H), 7.96 (br s, 1H), 7.94 (d, 1H), 7.93 (d, 1H), 7.30 (m, 1H), 7.18 (br s, 1H), 7.14 (m, 1H), 7.04 (d, 1H), 6.65 (ABq, 4H), 4.24 (m, 1H), 3.03 (dd, 1H), 2.88 (m, 1H), 2.57 (dd, 1H), 1.75 (s, 3H), 1.73 (s, 3H), 0.82 (d, 3H). LC-MS: m/e 530 (M+H)+ (3.8 min).

Workup

  1. customm/e 530 (M+H)+ (3.8 min)

Sources & evidence

ORD record
ord-46a295ec6cca42fcbc897669bba8f7b5
Source dataset
uspto-grants-2010_07
Patent number
US07754188B2

Reaction notes

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