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

HRID 455572노트

반응식

HRID 455572 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 11534Bromoacetonitrile4회HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)4회HCID 67383452(9-amino-7-bromo-4-fluoro-2-methoxy-9H-xanthen-9-yl)methanol

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-815140bcc91048b48c9e712d64879f42
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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