Water → 2-((9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methoxy)acetonitrile

HRID 455572ノート

反応式

HRID 455572 の反応式
[NH2:1][C:2]1([CH2:20][OH:21])[C:15]2[CH:14]=[C:13]([O:16][CH3:17])[CH:12]=[C:11]([F:18])[C:10]=2[O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:19])=[CH:6][CH:7]=2.CC(C)([O-])C.[Li+].Br[CH2:29][C:30]#[N:31].O>C1COCC1>[NH2:1][C:2]1([CH2:20][O:21][CH2:29][C:30]#[N:31])[C:15]2[CH:14]=[C:13]([O:16][CH3:17])[CH:12]=[C:11]([F:18])[C:10]=2[O:9][C:8]2[C:3]1=[CH:4][C:5]([Br:19])=[CH:6][CH:7]=2

参加物

6

反応物 4

HCID 962WaterHCID 11534Bromoacetonitrile4 回HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)4 回HCID 67383452(9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methanol

生成物 1

HCID 673828282-((9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methoxy)acetonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methanol (9.83 g, 27.8 mmol) in THF (46.3 mL) was sequentially treated with lithium t-butoxide (1 M in THF) (30.5 mL, 30.5 mmol) and 2-bromoacetonitrile (2.90 mL, 41.6 mmol) at RT. After 2.5 hours reaction time, additional 0.5 equivalent lithium t-butoxide and 2-bromoacetonitrile (1.5 mL) were added. After 4 hours reaction time, an additional 0.25 equivalent lithium t-butoxide and bromoacetonitrile (0.75 mL) were added. After 5 hours reaction time another 0.25 equivalent of lithium t-butoxide and bromoacetonitrile (0.75 mL) were added to the mixture. Water (100 ml) was added and solvents were removed under reduced pressure. The aqueous residue was filtered, the solid was washed twice with water, dried under reduced pressure and re-suspended in ethanol. The solid was filtered off, washed with ethanol and dried under reduced pressure to afford 2-((9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methoxy)acetonitrile.

後処理

  1. additionwere added
  2. customAfter 4 hours reaction time
  3. additionwere added to the mixture
  4. customsolvents were removed under reduced pressure
  5. filtrationThe aqueous residue was filtered
  6. washthe solid was washed twice with water
  7. customdried under reduced pressure
  8. filtrationThe solid was filtered off
  9. washwashed with ethanol
  10. customdried under reduced pressure

出典と根拠

ORDレコード
ord-815140bcc91048b48c9e712d64879f42
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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