Sodium Cyanide → HCID 56839770, compound

HRID 1466783Notes

Reaction equation

HRID 1466783 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([O:18][C:19]2[CH:20]=[C:21]([CH2:25]O)[CH:22]=[CH:23][CH:24]=2)=[C:9]1[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28]([N:31](CC)C(C)C)(C)C.CS(Cl)(=O)=O.[C-]#N.[Na+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([O:18][C:19]2[CH:20]=[C:21]([CH2:25][C:28]#[N:31])[CH:22]=[CH:23][CH:24]=2)=[C:9]1[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 56839548HCID 56839548, compound

Product 1

HCID 56839770HCID 56839770, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

[3-(1-Benzyl-6-chloro-2-methyl-1H-indol-3-yloxy)-phenyl]-methanol (0.092 g, 0.243 mmol) and N,N-diisopropylethylamine (3 μL, 0.486 mmol) were dissolved in DCM at 0° C. Methanesulfonyl chloride (28 μL, 0.365 mmol) was added and the reaction stirred for 5 minutes then sodium cyanide (0.024 g, 0.486 mmol) and DMF (2 mL) were added. The reaction was then concentrated under vacuum and DMF (2 mL) was added. The reaction was heated to 60° C. for 20 minutes then submitted to aqueous workup to give the title compound.

Workup

  1. concentrationThe reaction was then concentrated under vacuum and DMF (2 mL)
  2. additionwas added

Sources & evidence

ORD record
ord-3f053a904cd14c6b869be3ea7dbd80d5
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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