Pentane → HCID 67994896, compound

HRID 2361422Notes

Reaction equation

HRID 2361422 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8]3[CH2:11][CH2:12][N:13]([C:15]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:14][C:7]=3[C:6]=2[C:5]([Br:34])=[CH:4][CH:3]=1.C([Li])(C)(C)C.CCCCC.C[Si]([N:49]=[C:50]=[O:51])(C)C>C1COCC1.O>[Br:34][C:5]1[CH:4]=[CH:3][C:2]([C:50]([NH2:49])=[O:51])=[C:10]2[C:6]=1[C:7]1[CH2:14][N:13]([C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:12][CH2:11][C:8]=1[NH:9]2

Participants

7

Reactant 4

HCID 8003PentaneHCID 70696Trimethylsilyl isocyanateHCID 67994874HCID 67994874, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 67994896HCID 67994896, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 6,9-dibromo-2-trityl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (purity about 75%, 650 mg, 0.852 mmol) in THF (10 mL) was stirred at −78° C. and treated with tert-butyllithium, 1.7 M in pentane (2.505 mL, 4.26 mmol) over 2-3 min. After stirring for about 5-10 min at −78° C., the red-orange solution was stirred on an ice-water bath for 2 h. The solution was then cooled again to −78° C. and treated with trimethylsilyl isocyanate (0.922 mL, 6.81 mmol). Stirring was continued while allowing the cooling bath to warm slowly to room temperature. After 19 h, the mixture was treated with water (5 mL) and extracted twice with EtOAc. The combined organic phases were dried and concentrated. The residue was subjected to column chromatography on silica gel (80 g), eluting with EtOAc-hexane (gradient from 20:80 to 100:0) to provide the desired product as an off-white solid (251 mg, 55% yield). LCMS (M+H-trityl)+ m/z 294, 296.

Workup

  1. stirringthe red-orange solution was stirred on an ice-water bath for 2 h
  2. temperatureThe solution was then cooled again to −78° C.
  3. stirringStirring
  4. temperatureto warm slowly to room temperature
  5. waitAfter 19 h
  6. extractionextracted twice with EtOAc
  7. customThe combined organic phases were dried
  8. concentrationconcentrated
  9. washeluting with EtOAc-hexane (gradient from 20:80 to 100:0)

Sources & evidence

ORD record
ord-d6b2c5bd07ff4d7b8c3b751be4f6f5d5
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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