Dimethylformamide → HCID 66909223, compound

HRID 881648Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]1(C1C=C(F)C=C(F)C=1C#N)[F:15])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[C:33]([O:37][C:38](=[O:47])[NH:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([OH:46])[CH:41]=1)([CH3:36])([CH3:35])[CH3:34].C[N:49]([CH:51]=O)C>>[C:1]([O:5][C:6](=[O:26])[N:7]([C:11]1[CH:10]=[C:9]([F:15])[CH:8]=[C:13]([O:46][C:42]2[CH:43]=[CH:44][CH:45]=[C:40]([NH:39][C:38]([O:37][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:47])[CH:41]=2)[C:12]=1[C:51]#[N:49])[C:8]1[CH:13]=[CH:12][C:11]([I:14])=[CH:10][C:9]=1[F:15])([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 4

HCID 6228Dimethylformamide2×

HCID 10796Cesium carbonate

HCID 312485tert-butyl N-(3-hydroxyphenyl)carbamate

HCID 66909263HCID 66909263, compound

Product 1

HCID 66909223HCID 66909223, compound

Conditions

Temperature: 50 °C

Procedure

500 mg 2(2-Cyano-3,5-difluoro-phenyl)-(2-fluoro-4-iodo-phenyl)-carbamic acid tert-butyl ester (1.05 mmol, 1 eq.) and 412 mg Cs2CO3 (1.27 mmol, 1.2 eq) were dissolved in 5.5 mL DMF and treated with 265 mg (3-hydroxy-phenyl)-carbamic acid tert-butyl ester (1.27 mmol. 1.2 eq.) dissolved in 5.5 mL DMF. The resulting mixture is stirred at 50° C. for 16 h. Extractive workup provided a crude product containing the desired target compound as a mixture of regioisomers along with a smaller fraction of the product of double substitution. This mixture was advanced without further purification.

Sources & evidence

ORD record: ord-76d36ce967c44a36acda9438280eea94
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993630B2

Reaction notes

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