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

HRID 1912642ノート

反応式

HRID 1912642 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-43ee0bab69bd4c768253ff05d6a64669
出典データセット
uspto-grants-2013_12
特許番号
US08609653B2

反応ノート

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