Sodium hydride → HCID 58215764, compound

HRID 1661576Notes

Reaction equation

HRID 1661576 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=3)[CH:2]=1.[H-].[Na+].[C:20]([C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1)#[N:21]>CN(C=O)C>[C:20]([C:22]1[CH:23]=[C:24]([S:28]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1)#[N:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 445541352-pyridin-3-yl-1H-indole-5-carbonitrile

Product 1

HCID 58215764HCID 58215764, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-pyridin-3-yl-1H-indole-5-carbonitrile (Example 8, 300 mg, 1.37 mmol) at 0° C. in DMF (12 mL) is added 60% sodium hydride (82 mg, 2.06 mmol) and the mixture stirred for 10 min at 0° C. The reaction mixture is then warmed to room temperature and stirred for 30 min. 3-Cyanobenzenesulfonyl chloride (552 mg, 2.74 mmol) in DMF (2 mL) is added dropwise at 0° C. and the reaction is stirred at room temperature for 1 h. The reaction is quenched by adding water (1 mL). The resulting mixture is purified by HPLC X-bridge RP18 using acetonitrile-0.1% ammonia hydroxide as an eluent to yield 1-(3-cyano-benzenesulfonyl)-2-pyridin-3-yl-1H-indole-5-carbonitrile. 1H NMR (400 MHz, CDCl3) δ ppm 7.11 (s, 1H), 7.54 (dd, J=7.8, 4.8 Hz, 1H), 7.66 (dd, J=8.1, 2.0 Hz, 1H), 7.72 (t, J=7.7 Hz, 1H), 7.86 (dd, J=8.7, 1.6 Hz, 1H), 7.94 (t, J=1.5 Hz, 1H), 7.98 (dt, J=8.2, 2.0, 1.8 Hz, 1H), 8.16 (dd, J=7.6, 1.3 Hz, 1H), 8.19 (d, J=1.0 Hz, 1H), 8.34 (d, J=8.6 Hz, 1H), 8.67 (d, J=2.8 Hz, 1H), 8.71 (dd, J=4.9, 1.6 Hz, 1H). HRMS (ESI) m/z 385.0763 [(M+H)+ Calcd for C21H13N4O2S: 385.0759].

Workup

  1. temperatureThe reaction mixture is then warmed to room temperature
  2. stirringstirred for 30 min
  3. stirringthe reaction is stirred at room temperature for 1 h
  4. customThe reaction is quenched
  5. additionby adding water (1 mL)
  6. customThe resulting mixture is purified by HPLC X-bridge

Sources & evidence

ORD record
ord-70f3ed293eb049d1b64c6247a60bfbdf
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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