Morpholine → (6-Bromopyridin-3-YL)(morpholino)methanone

HRID 402954ノート

反応式

HRID 402954 の反応式
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[Br:1][C:2]1[N:3]=[CH:4][C:5]([C:6]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[O:8])=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2389326-Bromonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 65809001(6-Bromopyridin-3-YL)(morpholino)methanone収率 79%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

The mixture of 6-bromonicotinic acid (700 mg, 3.5 mmol), morpholine (391 mg, 4.5 mmol), HATU (220 mg, 0.59 mmol) and DIPEA (0.3 mL) in 10 mL of dry THF was stirred at room temperature for 14 hours. The reaction solution was evaporated to dryness. To the residue was added 20 mL of 0.5N hydrochloride, and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was dried over sodium sulfate and concentrated to give (6-bromopyridin-3-yl)(morpholino)methanone (750 mg, 79%). LC-MS: 271, 273 [M+H]+, tR=1.290 min.

後処理

  1. customThe reaction solution was evaporated to dryness
  2. additionTo the residue was added 20 mL of 0.5N hydrochloride
  3. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-9d71cb354a264a729e5186fd6e9343ee
出典データセット
uspto-grants-2014_06
特許番号
US08742098B2

反応ノート

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