P,P-Diphenylphosphinic azide → HCID 86679177, compound

HRID 1774826Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:8]2(C([O-])=O)[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.[K+].[F:15][C:16]1[CH:25]=[C:24]2[C:19]([CH2:20][CH2:21][C:22](=[O:27])[N:23]2[CH3:26])=[CH:18][C:17]=1B1OC(C)(C)C(C)(C)O1.C1(P([N:51]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C[Si](C)(C)[O-].[Na+]>>[NH2:51][C:8]1([C:4]2[CH:3]=[C:2]([C:17]3[CH:18]=[C:19]4[C:24](=[CH:25][C:16]=3[F:15])[N:23]([CH3:26])[C:22](=[O:27])[CH2:21][CH2:20]4)[CH:7]=[N:6][CH:5]=2)[CH2:9][CH2:10]1

Participants

Reactant 4

HCID 199401P,P-Diphenylphosphinic azide

HCID 23672319Sodium trimethylsilanolate

HCID 66788306HCID 66788306, compound

HCID 86679131HCID 86679131, compound

Product 1

HCID 86679177HCID 86679177, compound

Procedure

In analogy to the procedures described for the preparation of example 59, potassium 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate (example 59 [B]) has been reacted with 7-fluoro-1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-22) and subsequently with diphenylphosphoryl azide and sodium trimethylsilanolate to give the title compound as a light yellow oil. MS: 312.5 (M+H+).

Sources & evidence

ORD record: ord-897438b816ad4658bb416e7d9200c5ea
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260408B2

Reaction notes

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