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

HRID 857300

反応式

HRID 857300 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d250f205cf274b0fb1dbf8a9b43abdd5
出典データセット
uspto-grants-2006_12
特許番号
US07144896B2

関連ノート

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