2-Fluoropyridine-3-boronic acid → (S)-2'-(3,6-dihydro-2H-pyran-4-yl)-4'-fluoro-7'-(2-fluoropyridin-3-yl)-5,6-dihydrospiro[[1,3]oxazine-4,9'-xanthen]-2-amine

HRID 455738Notes

Reaction equation

HRID 455738 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.[F:25][C:26]1[C:31](B(O)O)=[CH:30][CH:29]=[CH:28][N:27]=1.[O:35]1[CH2:40][CH:39]=[C:38](B2OC(C)(C)C(C)(C)O2)[CH2:37][CH2:36]1>>[O:35]1[CH2:36][CH:37]=[C:38]([C:10]2[CH:9]=[C:8]([F:24])[C:7]3[O:6][C:5]4[C:14](=[CH:15][C:2]([C:31]5[C:26]([F:25])=[N:27][CH:28]=[CH:29][CH:30]=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)[CH2:39][CH2:40]1

Participants

4

Reactant 3

HCID 27832702-Fluoropyridine-3-boronic 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 58465933(S)-2'-(3,6-dihydro-2H-pyran-4-yl)-4'-fluoro-7'-(2-fluoropyridin-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, 2-fluoropyridin-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-4acb6fe0cc2c45a58d9f4f7cd1ceac31
Source dataset
uspto-grants-2013_07
Patent number
US08497264B2

Reaction notes

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