Water → HCID 70938331, compound

HRID 1041886Notes

Reaction equation

HRID 1041886 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.[CH3:25][C:26]1([CH3:40])[C:30]([CH3:32])([CH3:31])[O:29][B:28]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[O:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>C(Cl)Cl>[CH3:16][C:4]1[CH:5]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH:7]=[C:2]([CH3:1])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH:37][C:36]2[CH:38]=[CH:39][C:33]([B:28]3[O:27][C:26]([CH3:40])([CH3:25])[C:30]([CH3:31])([CH3:32])[O:29]3)=[CH:34][CH:35]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 593426022',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)biphenyl-3-carbaldehyde

Product 1

HCID 70938331HCID 70938331, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2′,6′-dimethyl-4′-(3-(methylsulfonyl)propoxy)-[1,1′-biphenyl]-3-carbaldehyde (1.0 g) synthesized according to a method described in [WO 2008/001931 pamphlet, (Reference Example 18)] and 4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.63 g) were dissolved in methylene chloride (10 mL), and to the resultant solution, sodium triacetoxyborohydride (1.84 g) was added, followed by stirring the resultant reaction mixture at room temperature for 14 hours. To the reaction mixture, water (20 mL) was added, followed by extracting the reaction mixture with methylene chloride (20 mL) twice, and the resultant organic phase was washed sequentially with water (50 mL) and a saturated saline (50 mL) and was dried over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure to obtain the subject compound (1.4 g) as a colorless amorphous solid.

Workup

  1. customreaction mixture at room temperature for 14 hours
  2. extractionby extracting the reaction mixture with methylene chloride (20 mL) twice
  3. washthe resultant organic phase was washed sequentially with water (50 mL)
  4. dry with materiala saturated saline (50 mL) and was dried over anhydrous sodium sulfate
  5. distillationFrom the organic phase, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e2a5f61a618c4137aa143ea450bb179e
Source dataset
uspto-grants-2013_10
Patent number
US08557766B2

Reaction notes

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