2-((3R,3aR,6R,6aS)-6-(tert-butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-5-iodo-3-((2-(tri-methylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine → HCID 178455386, compound

HRID 715571Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:21]4=[N:22][C:23](I)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC1(C)C(C)(C)OB([C:45]2[CH:50]=[CH:49][C:48]([C@H:51]3[CH2:56][CH2:55][C@H:54]([OH:57])[CH2:53][CH2:52]3)=[CH:47][CH:46]=2)O1>>[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:21]4=[N:22][C:23]([C:45]5[CH:50]=[CH:49][C:48]([C@H:51]6[CH2:52][CH2:53][C@H:54]([OH:57])[CH2:55][CH2:56]6)=[CH:47][CH:46]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 1234546122-((3R,3aR,6R,6aS)-6-(tert-butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-5-iodo-3-((2-(tri-methylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine

HCID 178431056HCID 178431056, compound

Product 1

HCID 178455386HCID 178455386, compound

Procedure

The title compound is prepared from 2-((3R,3aR,6R,6aS)-6-(tert-butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-5-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine and (trans)-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexanol following a procedure analogous to that described for Intermediate 7 Step 2. LC (method 5): tR=1.16 min; Mass spectrum (ESI+): m/z=716 [M+H]+.

Sources & evidence

ORD record: ord-6e97614f8d4541dc88f35ee1c2b848bc
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187477B2

Reaction notes

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