Dimethylformamide → tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate

HRID 1678731

反応式

HRID 1678731 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:4][N:3]=1.C([Li])(C)(C)C.CCCCC.CN([CH:29]=[O:30])C>C1COCC1>[Cl:1][C:2]1[C:7]([CH:29]=[O:30])=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 21858447tert-butyl N-(2-chloropyridin-4-yl)carbamateHCID 178446069HCID 178446069、化合物

生成物 1

HCID 52987944tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl (2-chloropyridin-4-yl)carbamate (1.14 gm, 5 mmol) in dry THF (20 mL) was cooled to −70° C. under an inert atmosphere and 1.7 M t-butyl lithium/pentane (8 mL, 13.5 mmol) was slowly added. The reaction was stirred for two hours and then dry DMF (1.2 mL, 15.5 mmol) was added. The reaction was allowed to slowly warm to room temperature over a three hour period. The reaction mixture was quenched with 3 N HCl (12 mL) and diluted with diethyl ether. The ether layer was washed with aqueous NaHCO3, dried (over Na2SO4), filtered and evaporated. The residue was triturated with cold diethyl ether to give pure t-butyl (2-chloro-3-formylpyridin-4-yl)carbamate. The mother liquors were chromatographed on silica gel eluting with 15-20% ethyl acetate/hexane to give additional product. 1H-NMR (500 MHz, CDCl3): δ11.0 (1H, br s), 10.52 (1H, s), 8.38 (1H, d, J=6 Hz), 8.31 (1H, d, J=6 Hz), 1.54 (9H, s); m/e (m+1): 257.2.

後処理

  1. additionwas slowly added
  2. customThe reaction mixture was quenched with 3 N HCl (12 mL)
  3. additiondiluted with diethyl ether
  4. washThe ether layer was washed with aqueous NaHCO3
  5. dry with materialdried (over Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was triturated with cold diethyl ether

出典と根拠

ORDレコード
ord-bc7fc61fcaff484f874ef14c219cdbf3
出典データセット
uspto-grants-2011_08
特許番号
US08008317B2

関連ノート

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