2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(1H-pyrazol-4-yl)-1,2-benzoxazole-5-carbaldehyde

HRID 245539Notes

Reaction equation

HRID 245539 reaction equation
[NH:1]1[CH:5]=[C:4](B(O)O)[CH:3]=[N:2]1.Cl[C:10]1[C:14]2[CH:15]=[C:16]([CH:28]=[O:29])[C:17]([N:20]3[CH2:25][C@H:24]([CH3:26])[O:23][C@H:22]([CH3:27])[CH2:21]3)=[C:18]([F:19])[C:13]=2[O:12][N:11]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:27][C@H:22]1[O:23][C@@H:24]([CH3:26])[CH2:25][N:20]([C:17]2[C:16]([CH:28]=[O:29])=[CH:15][C:14]3[C:10]([C:4]4[CH:3]=[N:2][NH:1][CH:5]=4)=[N:11][O:12][C:13]=3[C:18]=2[F:19])[CH2:21]1

Participants

5

Reactant 3

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 177502781H-Pyrazole-4-boronic acidHCID 866581213-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde2×

Product 1

HCID 1363608266-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(1H-pyrazol-4-yl)-1,2-benzoxazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

1H-pyrazole-4-boronic acid pinacolate ester, 3-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde (Intermediate 534), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and tris(dibenzylideneacetone)dipalladium(0) were reacted using a method similar to the one described for the synthesis of Intermediate 554.

Sources & evidence

ORD record
ord-197d0a37983d4abd9b1fa5cedb096b95
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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