HCID 52952226, compound → HCID 15602994, compound

HRID 1784875Notes

Reaction equation

ClC1C=C(NC(=O)C)C=C(S(C2C=NC=CC=2)(=O)=O)C=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([S:27]([C:30]2[CH:31]=[C:32]([NH:55][C:56](=[O:58])[CH3:57])[CH:33]=[C:34]([C:36]3[CH:44]=[CH:43][CH:42]=[C:41]4[C:37]=3[CH:38]=[CH:39][N:40]4[Si](C(C)C)(C(C)C)C(C)C)[CH:35]=2)(=[O:29])=[O:28])[CH:22]=1>>[NH:40]1[C:41]2[C:37](=[C:36]([C:34]3[CH:33]=[C:32]([NH:55][C:56](=[O:58])[CH3:57])[CH:31]=[C:30]([S:27]([C:23]4[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=4)(=[O:29])=[O:28])[CH:35]=3)[CH:44]=[CH:43][CH:42]=2)[CH:38]=[CH:39]1

Participants

Reactant 2

HCID 52952226HCID 52952226, compound

HCID 52952227HCID 52952227, compound

Product 1

HCID 15602994HCID 15602994, compound

Procedure

N-[3-chloro-5-(pyridine-3-sulfonyl)-phenyl]-acetamide was converted to N-[3-(pyridine-3-sulfonyl)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-acetamide and the triisopropylsilyl protecting group was removed as described in Example 35. 1H NMR (400 MHz, CD3OD): δ 9.17 (br s, 1H), 8.82 (br s, 1H), 8.38 (d, J=8.4 Hz, 1H), 8.30 (s, 1H), 8.12 (s, 1H), 7.96 (d, J=1.4 Hz, 1H), 7.63 (s, 1H), 7.44 (d, J=8.2 Hz, 1H), 7.31 (d, J=3.3 Hz, 1H), 7.19 (t, J=7.7 Hz, 1H), 7.10 (d, J=7.4 Hz, 1H), 6.53 (d, J=3.2 Hz, 1H), 2.15 (s, 3H).

Workup

customthe triisopropylsilyl protecting group was removed

Sources & evidence

ORD record: ord-40e908d8e8294628a4cc1ff4ee50fefd
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504401B2

Reaction notes

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