3-Pyridinylboronic acid → (S)-2'-(3,6-dihydro-2H-pyran-4-yl)-4'-flouro-7'-(pyridin-3-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

HRID 1472479Notes

Reaction equation

HRID 1472479 reaction equation
Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][C:7]3[C:8]([F:24])=[CH:9][C:10](OC)=[CH:11][C:12]=3[C@@:13]32[CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]3)=[CH:4][CH:3]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.[O:34]1[CH2:39][CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH2:36][CH2:35]1>>[O:34]1[CH2:35][CH:36]=[C:37]([C:10]2[CH:9]=[C:8]([F:24])[C:7]3[O:6][C:5]4[C:14](=[CH:15][C:2]([C:27]5[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=5)=[CH:3][CH:4]=4)[C@@:13]4([CH2:20][CH2:19][O:18][C:17]([NH2:21])=[N:16]4)[C:12]=3[CH:11]=2)[CH2:38][CH2:39]1

Participants

4

Reactant 3

HCID 27343783-Pyridinylboronic acidHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 58465963(S)-7'-bromo-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

Product 1

HCID 58465981(S)-2'-(3,6-dihydro-2H-pyran-4-yl)-4'-flouro-7'-(pyridin-3-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

Procedure

The title compound was synthesized by steps analogous to those described in method A7 above, but using intermediate 20B, pyridin-3-ylboronic acid and 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Sources & evidence

ORD record
ord-d401214616924f54ad409d65cf657b3a
Source dataset
uspto-grants-2015_04
Patent number
US09012446B2

Reaction notes

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