(4-Bromophenyl)boronic acid → (3R,3aR,6R,6aR)-6-(5-(4-Bromophenyl)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 715583Notes

Reaction equation

HRID 715583 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:11]=[C:10]([O:12][C@H:13]3[C@H:17]4[O:18][CH2:19][C@@H:20]([OH:21])[C@H:16]4[O:15][CH2:14]3)[N:9]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:5]2=[N:6][C:7]=1I.[Br:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1>>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([C:7]2[N:6]=[C:5]3[N:9]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:10]([O:12][C@H:13]4[C@H:17]5[O:18][CH2:19][C@@H:20]([OH:21])[C@H:16]5[O:15][CH2:14]4)=[N:11][C:4]3=[CH:3][C:2]=2[Cl:1])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 79599(4-Bromophenyl)boronic acidHCID 123413447(3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 123535639(3R,3aR,6R,6aR)-6-(5-(4-Bromophenyl)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol

Procedure

The title compound is prepared from (3R,3aR,6R,6aR)-6-(6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-2-yloxy)hexahydrofuro[3,2-b]furan-3-ol and 4-bromophenylboronic acid following a procedure analogous to that described for Intermediate 3. LC (method 2): tR=1.24 min; Mass spectrum (ESI+): m/z=582 [M+H]+.

Sources & evidence

ORD record
ord-e5421ae71f39449ba9bdd4f5817eef65
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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