2-(2-Fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 86665942, compound

HRID 2406392Notes

Reaction equation

HRID 2406392 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12](I)=[C:13]2[C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C:19]=3[S:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:28]=1B1OC(C)(C)C(C)(C)O1>>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([C:28]2[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:27]=2[F:26])=[C:13]2[C:20]3[CH2:21][CH2:22][CH2:23][CH2:24][C:19]=3[S:18][C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 696724352-(2-Fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 69673123Methyl (2S)-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate

Product 1

HCID 86665942HCID 86665942, compound

Procedure

The title compound was prepared from Methyl (2S)-tert-butoxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 16, 100 mg, 212 μmol) and 2-(2-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 19, 99 mg, 424 μmol) using the same method as described in Example 44, Step 1 to yield 100 mg, 96%. Material obtained was a mixture of atropisomers, in a 2:1 ratio.

Workup

  1. customto yield 100 mg, 96%
  2. customMaterial obtained
  3. additiona mixture of atropisomers

Sources & evidence

ORD record
ord-3c9a86b70955453784be8415eed0fa11
Source dataset
uspto-grants-2014_08
Patent number
US08809363B2

Reaction notes

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