2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(3,6-dihydro-2H-thiopyran-4-yl)-furo[3,2-c]pyridin-6-ylamine

HRID 911966Notes

Reaction equation

HRID 911966 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.[S:24]1[CH2:29][CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH2:26][CH2:25]1>>[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:27]3[CH2:28][CH2:29][S:24][CH2:25][CH:26]=3)[C:6]=2[CH:7]=[N:8][C:9]=1[NH2:23])[CH3:13]

Participants

3

Reactant 2

HCID 467397352-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 578127253-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 578125037-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(3,6-dihydro-2H-thiopyran-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 2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane. 1H-NMR (CDCl3, 400 MHz): 6=1.79 (d, J=6.8 Hz, 3H), 2.47-2.68 (m, 2H), 2.82 (t, J=5.8 Hz, 2H), 3.20-3.46 (m, 2H), 4.68 (br. s., 2H), 6.31-6.38 (m, 1H), 6.44 (q, J=6.7 Hz, 1H), 6.97 (t, J=8.5 Hz, 1H), 7.30 (s, 1H), 8.14 (s, 1H). MS (ES+): m/z (MH+, 35Cl, 37Cl), 440.94 (MH+, 37Cl, 37Cl). HPLC: tR=3.69 min (polar—5 min, ZQ3).

Workup

  1. customHPLC: tR=3.69 min (polar—5 min, ZQ3)

Sources & evidence

ORD record
ord-7623ceff04f540e79a998dd5a1308c68
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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