3,6-Dihydro-2H-pyran-4-boronic acid pinacol ester → 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(3,6-dihydro-2H-pyran-4-yl)-furo[3,2-c]pyridin-6-ylamine

HRID 911965Notes

Reaction equation

HRID 911965 reaction equation
Br[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:23])=[C:10]([O:11][C@@H:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[C:5]=2[O:4][CH:3]=1.CC1(C)C(C)(C)OB([C:32]2[CH2:33][CH2:34][O:35][CH2:36][CH:37]=2)O1>>[Cl:22][C:15]1[C:16]([F:21])=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[C@H:12]([O:11][C:10]1[C:5]2[O:4][CH:3]=[C:2]([C:32]3[CH2:37][CH2:36][O:35][CH2:34][CH:33]=3)[C:6]=2[CH:7]=[N:8][C:9]=1[NH2:23])[CH3:13]

Participants

3

Reactant 2

HCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 578127253-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 578124297-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(3,6-dihydro-2H-pyran-4-yl)-furo[3,2-c]pyridin-6-ylamine

Procedure

The title compound was prepared according to General procedure A with starting materials 3-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-furo[3,2-c]pyridin-6-ylamine and 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran. 1H-NMR (CDCl3, 400 MHz): δ=1.86 (d, 3H), 2.40-2.52 (m, 2H), 3.94 (t, J=5.6 Hz, 2H), 4.36 (q, J=2.5 Hz, 2H), 4.77 (br. s., 2H), 6.24 (br. s., 1H), 6.52 (q, J=6.6 Hz, 1H), 7.01-7.10 (m, 1H), 7.29 (t, 1H), 7.37 (s, 1H), 8.24 (s, 1H). MS (ES+): m/z 423.02 (MH+, 35Cl, 37Cl), 424.94 (MH+, 37Cl, 37Cl). HPLC: tR=3.34 min (polar—5 min, ZQ3).

Workup

  1. customHPLC: tR=3.34 min (polar—5 min, ZQ3)

Sources & evidence

ORD record
ord-d025d61458d54d41b6906f948385e9e3
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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