Ethanol → HCID 86721353, compound

HRID 869524Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:33]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[C:29]([OH:30])[C:24]=4[N:23]=[C:22]3[CH2:31][OH:32])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].[CH2:34](O)[CH3:35]>>[CH2:34]([O:30][C:29]1[C:24]2[N:23]=[C:22]([CH2:31][OH:32])[N:21]([CH2:20][C:18]3[CH:17]=[CH:16][C:10]4/[C:11](=[C:12](/[CH3:15])\[C:13]#[N:14])/[C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:33][C:6]=5[O:7][CH2:8][C:9]=4[CH:19]=3)[C:25]=2[CH:26]=[CH:27][CH:28]=1)[CH3:35]

Participants

Reactant 2

HCID 702Ethanol

HCID 86721349HCID 86721349, compound

Product 1

HCID 86721353HCID 86721353, compoundYield 50%

Procedure

[step 1] Using (E)-2-(3-fluoro-8-{[4-hydroxy-2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}dibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (201 mg, 0.46 mmol) obtained in Reference Example 2A, step 4, and ethanol (0.27 mL, 4.55 mmol) instead of deuterated methanol, and in the same manner as in Reference Example 2A, step 5, (E)-2-(8-{[4-ethoxy-2-(hydroxymethyl)-1H-benzo[d]imidazol-1-yl]methyl}-3-fluorodibenzo[b,e]oxepin-11(6H)-ylidene)propanenitrile (107 mg, 50%) was obtained.

Sources & evidence

ORD record: ord-f535e33be66e4cda8c4a341d3fcf0ba3
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969345B2

Reaction notes

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