Sodium Carbonate → 6-(4-Carboxyphenyl)-8-(4-benzo[c]furazanyl)-1,7-naphthyridine

HRID 369038

반응식

HRID 369038 반응식
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18](Br)[N:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([OH:3])=[O:2].[N:21]1[O:22][N:23]=[C:24]2[C:29](B(O)O)=[CH:28][CH:27]=[CH:26][C:25]=12.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:17](=[C:18]([C:29]4[C:24]5[C:25](=[N:21][O:22][N:23]=5)[CH:26]=[CH:27][CH:28]=4)[N:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)=[CH:6][CH:5]=1)([OH:3])=[O:2]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 80271Tri-o-tolylphosphineHCID 21186805B-2,1,3-Benzoxadiazol-4-ylboronic acidHCID 232846464-(8-Bromo-1,7-naphthyridin-6-yl)benzoic acid

생성물 1

HCID 232846386-(4-Carboxyphenyl)-8-(4-benzo[c]furazanyl)-1,7-naphthyridine수율 60.7%

시약·촉매·용매 2

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 6-(4-carboxyphenyl)-8-bromo-1,7-naphthyridine (100 mg, 0.304 mmol) in DMF (2.5 ml) is added 4-benzo[c]furazanyl boronic acid (60 mg, 0.36 mmol), bis(dibenzylidenacetone) palladium (7 mg, 0.0122 mmol), tri-o-tolylphosphine (7.4 mg, 0.024 mmol) and aqueous Na2CO3 (0.9 ml, 2N). The reaction mixture is stirred at 80° for 2 h. The hot solution is filtred through cellit and the solution evaporated to dryness. The residue is stirred in ethyl acetate (20 ml), the suspension is filtered and the organic solvent is removed. The residue is dissolved in hot DMF (7 ml) and the crude product is precipitated by carefully adding aqueous HCl (2N, 1 ml). The crude product in recrystallized from hot DMF to yield the title compound (68 mg). MH+369; Melting point >300° C. M+H=369. Retention time HPLC=10.40 min (column: LiChroCart 125-4, Supersphere 60 RP-select B, 40°; eluent: acetonitril-water (0.1% TFA)=45:55; 1 ml/min; detection at 254 nm).

후처리

  1. customthe solution evaporated to dryness
  2. stirringThe residue is stirred in ethyl acetate (20 ml)
  3. filtrationthe suspension is filtered
  4. customthe organic solvent is removed
  5. dissolutionThe residue is dissolved in hot DMF (7 ml)
  6. customthe crude product is precipitated by carefully adding aqueous HCl (2N, 1 ml)
  7. customThe crude product in recrystallized from hot DMF

출처 및 근거

ORD 기록
ord-3e909dee7bf24e4f821be6c1c311f31c
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136821

연결된 노트

불러오는 중…