Borane → 6-bromo-8-fluoro-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 1912642노트

반응식

HRID 1912642 반응식
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:5]2[O:6][CH2:7][C:8](=O)[NH:9][C:4]=2[C:3]=1[CH3:14].B>O1CCCC1>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:5]2[O:6][CH2:7][CH2:8][NH:9][C:4]=2[C:3]=1[CH3:14]

참가 물질

4

반응물 2

HCID 6331BoraneHCID 712091776-bromo-8-fluoro-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

생성물 1

HCID 712092976-bromo-8-fluoro-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine수율 93.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

An ice cold mixture of 6-bromo-8-fluoro-5-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (510 mg, 1.961 mmol) in Tetrahydrofuran (THF) (8 mL) was treated with borane 1M in THF (2.94 mL, 2.94 mmol) (1.5 eq) and then stirred at ambient temperature for 150 minutes. The mixture was cooled to 0° C. and then quenched slowly with 1N NaOH (5 mL×10). The mixture was extracted with ethyl acetate, washed with 1N NaOH, dried over sodium sulfate, filtered and then concentrated to afford 6-bromo-8-fluoro-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine (450 mg) as a light brown solid which was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) d=6.77 (d, J=10.1 Hz, 1 H), 4.28-4.25 (m, 2 H), 3.77 (br. s., 1 H), 3.52 (m, 2 H), 2.16 (s, 3 H); LC/MS (m/z) ES+=245.99 (M+1).

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. customquenched slowly with 1N NaOH (5 mL×10)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with 1N NaOH
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-43ee0bab69bd4c768253ff05d6a64669
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609653B2

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