Hydrochloric Acid → 4-Fluoro-3-(6-isopropyl-quinolin-8-yl)-benzoic acid

HRID 857300

반응식

HRID 857300 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.OB(O)[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[F:22])[C:16]([OH:18])=[O:17].C([O-])([O-])=O.[Na+].[Na+].Cl.[CH2:31](O)[CH2:32][CH3:33]>[NH4+].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:22][C:21]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[C:9]1[CH:8]=[C:7]([CH:32]([CH3:33])[CH3:31])[CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 7047QuinolineHCID 10340Sodium CarbonateHCID 218655933-Borono-4-fluorobenzoic acid

생성물 1

HCID 218655434-Fluoro-3-(6-isopropyl-quinolin-8-yl)-benzoic acid

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 25517Ammonium Chloride용매

실험 절차

A mixture of Quinoline 1 (1.0 eq), the 3-dihydroxylboranyl-4-fluoro-benzoic acid from Step 1 (1.2 eq), Pd(PPh3)4 (0.05 eq) and aqueous Na2CO3 (2.0M; 4.0 eq) in propanol (0.1M) was stirred at 90° C. for 12 h. The resulting mixture was cooled to room temperature, poured in saturated aqueous NH4Cl, the pH was adjusted to 5 with HCl (10%) and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered. Upon concentration the desired compound crystallized and was isolated by filtration.

후처리

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationUpon concentration the desired compound
  6. customcrystallized
  7. customwas isolated by filtration

출처 및 근거

ORD 기록
ord-d250f205cf274b0fb1dbf8a9b43abdd5
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144896B2

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