[1-(tert-Butoxycarbonyl)-5-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-2-yl]boronic acid → HCID 59224758, compound

HRID 2078748Notes

Reaction equation

HRID 2078748 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH2:16][O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:15][C:11]=2[C:10](I)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]([Si:30]([CH3:52])([CH3:51])[O:31][C:32]1[CH:40]=[C:39]2[C:35]([CH:36]=[C:37](B(O)O)[N:38]2[C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])=[CH:34][CH:33]=1)([CH3:29])([CH3:28])[CH3:27].C([Si](C)(C)OC1C=C2C(=CC=1)N(C(OC(C)(C)C)=O)C(B(O)O)=C2)(C)(C)C>>[C:44]([O:43][C:41]([N:38]1[C:39]2[C:35](=[CH:34][CH:33]=[C:32]([O:31][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:51])[CH3:52])[CH:40]=2)[CH:36]=[C:37]1[C:10]1[C:11]2[S:15][C:14]([CH2:16][O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][C:12]=2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[N:9]=1)=[O:42])([CH3:47])([CH3:46])[CH3:45]

Participants

4

Reactant 3

HCID 22285134[1-(tert-Butoxycarbonyl)-5-{[tert-butyl(dimethyl)silyl]oxy}-1H-indol-2-yl]boronic acidHCID 230924981-(1,1-Dimethylethyl) 2-borono-6-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1H-indole-1-carboxylateHCID 57637370HCID 57637370, compound

Product 1

HCID 59224758HCID 59224758, compound

Procedure

2-(5-Benzyloxymethyl-1-tert-butoxycarbonyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester [Intermediate (92)] was prepared in 39% yield using procedures similar to those of Example 5C, substituting 5-benzyloxymethyl-3-iodo-thieno[3,2-c]pyrazole-1-carboxylic acid tert-butyl ester [Intermediate (91)] for 3-iodo-thieno[3,2c]pyrazole-1-carboxylic acid tert-butyl ester and 6-(tert-butyl-dimethyl-silanoxy)-1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid [Intermediate (74), prepared by the application of method described in Example 4-6 of International Patent Application Publication No. WO 02/32861] for 5-(tert-butyl-dimethyl-silanoxy)-1-(tert-butoxycarbonyl)-1H-indole-2-boronic acid.

Workup

  1. customprepared by the application of method

Sources & evidence

ORD record
ord-a394a57b5dab4730be1a70eaadec22c9
Source dataset
uspto-grants-2011_04
Patent number
US07928231B2

Reaction notes

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