tert-Butanol → HCID 67043319, compound

HRID 217273Notes

Reaction equation

HRID 217273 reaction equation
[C:1]([OH:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]([F:18])([F:17])[C:8]1[CH:16]=[CH:15][C:11](C(O)=O)=[CH:10][N:9]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C>>[C:1]([O:5][C:41](=[O:26])[NH:38][C:11]1[CH:10]=[N:9][C:8]([C:7]([Cl:6])([F:17])[F:18])=[CH:16][CH:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 40427098HCID 40427098, compound

Product 1

HCID 67043319HCID 67043319, compound

Procedure

Under a nitrogen atmosphere, a solution of tert-butanol (100 ml), molecular sieve powder (4 angstrom) (23 g) and triethylamine was prepared (9.36 ml). After stirring for 5 minutes at ambient temperature, the compound obtained in Step A (10 g) was added, followed by diphenyl phosphoryl azide (16.3 g). The reaction mixture was heated to reflux for 3 hours and then filtered on Celite®. The reaction mixture was poured into water and extracted several times with diethyl ether. The combined organic layers were washed with brine, dried over sodium sulfate and then concentrated in vacuo. Chromatography on silica gel (eluent: hexane/ethyl acetate 5:1) afforded [6-(chlorodifluoromethyl)-pyridin-3-yl]-carbamic acid tert-butyl ester (10.6 g). MS (ES+) 279/281 (MH+); 1H NMR (400 MHz, CDCl3) 1.55 (s, 9H), 7.52 (d, 1H), 8.19 (m, 1H), 8.47 (d, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationfiltered on Celite®
  4. additionThe reaction mixture was poured into water
  5. extractionextracted several times with diethyl ether
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a47821344bff4350b600c4c50619a97b
Source dataset
uspto-grants-2012_06
Patent number
US08193362B2

Reaction notes

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