Hydrochloric Acid → HCID 58408280, compound

HRID 2192285Notes

Reaction equation

HRID 2192285 reaction equation
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([S:18]([C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH2:13][CH2:12]3)[O:3]1.I([O-])(=O)(=O)=O.[Na+].Cl>O1CCCC1.O>[OH:5][B:4]([OH:3])[C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:13][CH2:12]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23667635Sodium periodateHCID 58408293HCID 58408293, compound

Product 1

HCID 58408280HCID 58408280, compoundYield 133.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2.76 g 4-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile and 4.32 g sodium periodate were dissolved in a mixture of 45 ml tetrahydrofuran and 15 ml water. The mixture was stirred at room temperature for two hours. Then 2 ml 4M hydrochloric acid was added and the mixture stirred at room temperature for one hour. 150 ml water were added and the mixture extracted three times with portions of 50 ml ethyl acetate. The combined organic extracts were dried over MgSO4 and the solvent removed in vacuo to obtain 2.94 g of crude 4-(5-Dihydroxyboranyl-2,3-dihydro-indole-1-sulfonyl)-benzonitrile. This material was used without further purification.

Workup

  1. stirringthe mixture stirred at room temperature for one hour
  2. extractionthe mixture extracted three times with portions of 50 ml ethyl acetate
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-c634341e89b34a3aab1a9c316c9b9d61
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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