tert-Butanol → HCID 67355878, compound

HRID 2405102Notes

Reaction equation

HRID 2405102 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.CC[N:20]([CH2:23]C)CC.[CH3:25][S:26]([CH2:29][N:30]1[C:38]2[CH:37]=[C:36](C(O)=O)[N:35]=[CH:34][C:33]=2[CH:32]=[CH:31]1)(=[O:28])=[O:27].[CH3:42][C:43]([OH:46])([CH3:45])[CH3:44]>>[CH3:25][S:26]([CH2:29][N:30]1[C:38]2[CH:37]=[C:36]([NH:20][C:23](=[O:8])[O:46][C:43]([CH3:45])([CH3:44])[CH3:42])[N:35]=[CH:34][C:33]=2[CH:32]=[CH:31]1)(=[O:27])=[O:28]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67352882HCID 67352882, compound

Product 1

HCID 67355878HCID 67355878, compoundYield 50%

Procedure

A mixture of diphenylphosphoryl azide (1.1 g, 3.8 mmol), Et3N (1.8 ml, 13 mmol) and 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridine-6-carboxylic acid (8C, 650 mg, 2.6 mmol) in 2-methylpropan-2-ol (10 g, 140 mmol) was stirred at room temperature for 1 h and then at 80° C. for 3 h. The mixture was extracted with EtOAc/H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude mixture was purified by chromatography (SiO2, hexane:EtOAc=50:50) to give tert-butyl 1-(methylsulfonylmethyl)-1H-pyrrolo[3,2-c]pyridin-6-ylcarbamate (8D, 410 mg, 1.3 mmol, 50% yield) as a white powder. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.35-0.44 (m, 2H) 0.57-0.70 (m, 2H) 1.19-1.33 (m, 1H) 1.57 (s, 9H) 3.97 (d, J=6.82 Hz, 2H) 6.52-6.54 (m, 1H) 7.19 (d, J=3.28 Hz, 1H) 7.59 (br. s., 1H) 7.93 (s, 1H) 8.56 (d, J=1.01 Hz, 1H).

Workup

  1. waitat 80° C. for 3 h
  2. extractionThe mixture was extracted with EtOAc/H2O
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by chromatography (SiO2, hexane:EtOAc=50:50)

Sources & evidence

ORD record
ord-b8697e64a9d946b7b4ab49ef8352f683
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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