Water → 6-chloro-7-cyclopropylmethoxy-8-nitro-9H-beta-carboline

HRID 552191Notes

Reaction equation

HRID 552191 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:8][C:9]1[CH:10]=[C:11]2[C:19](=[C:20]([N+:23]([O-:25])=[O:24])[C:21]=1F)[NH:18][C:17]1[CH:16]=[N:15][CH:14]=[CH:13][C:12]2=1.O>CN(C=O)C>[Cl:8][C:9]1[CH:10]=[C:11]2[C:19](=[C:20]([N+:23]([O-:25])=[O:24])[C:21]=1[O:5][CH2:4][CH:1]1[CH2:3][CH2:2]1)[NH:18][C:17]1[CH:16]=[N:15][CH:14]=[CH:13][C:12]2=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 671651746-chloro-7-cyclopropylmethoxy-8-nitro-9H-beta-carbolineYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropylmethyl alcohol (0.921 ml, 11.4 mmol) was added to a stirring suspension of NaH (455 mg, 11.4 mmol) in DMF (20 ml) under an argon atmosphere. The resulting solution was allowed to stir at RT for 20 min. 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.9 mmol) was added to the stirring solution and the resulting mixture was allowed to stir at RT. Upon addition of H2O, a brown solid precipitated out which was filtered to give the desired 6-chloro-7-cyclopropylmethyoxy-8-nitro-9H-β-carboline (510 mg, 85%). 1H-NMR (300 MHz, DMSO-d6): δ 0.35 (m, 2H), 0.59 (m, 2H), 1.32 (m, 1H), 4.04 (d, 2H), 8.21 (d, 1H), 8.46 (d, 1H), 8.90 (s, 1H), 9.02 (s, 1H), 12.32 (b, 1H). Retention Time (LC, method: ammonium acetate standard): 2.63 min. MS (M+H+): 318.

Workup

  1. stirringto stir at RT
  2. customa brown solid precipitated out which
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-73de563950e54f3a8a473ab1f9c7e3c2
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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