Potassium Phosphate, Tribasic → US10023592, Example 259

HRID 518474노트

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HRID 518474 반응식
[CH3:1][N:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[C:5]2[CH:17]=[CH:18][O:19][C:4]=2[C:3]1=[O:20].[CH:21]1([CH2:24][O:25][C:26]2[C:27](I)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:23][CH2:22]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:21]1([CH2:24][O:25][C:26]2[C:27]([C:6]3[C:5]4[CH:17]=[CH:18][O:19][C:4]=4[C:3](=[O:20])[N:2]([CH3:1])[CH:7]=3)=[N:28][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:30][CH:31]=2)[CH2:22][CH2:23]1

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 1180225163-(Cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridineHCID 1240169906-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one

생성물 1

HCID 118021483US10023592, Example 259수율 62.3%

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of 6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furo[2,3-c]pyridin-7-one (50 mg, 0.18 mmol), 3-(cyclopropylmethoxy)-2-iodo-6-methylsulfonylpyridine (53 mg, 0.15 mmol), K3PO4 (114 mg, 0.54 mmol), Pd(dppf)Cl2 (13 mg, 0.018 mmol) in dioxane (5 mL) was bubbled with nitrogen for 5 min and then stirred at 70° C. for 12 h. The reaction mixture was concentrated, treated with DCM (30 mL), washed with water (30 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC to give the title compound (35 mg, yield: 52%) as an off-white solid.

후처리

  1. customwas bubbled with nitrogen for 5 min
  2. concentrationThe reaction mixture was concentrated
  3. additiontreated with DCM (30 mL)
  4. washwashed with water (30 mL) and brine (30 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by prep-HPLC

출처 및 근거

ORD 기록
ord-c39d564df8e24039aa2f0c6799d6331d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115114B2

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