3-Pyridinemethanol,alpha-ethynyl-(9CI) → HCID 9820757, compound

HRID 428671Notes

Reaction equation

HRID 428671 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[C:3]#[CH:4].Br[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1/[C:14](=[CH:22]/[C:23]1[NH:24][CH:25]=[CH:26][C:27]=1[O:28][CH3:29])/[C:15](=[O:21])[NH:16]2>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.CN(C=O)C.CCN(CC)CC>[OH:1][CH:2]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][CH:10]=1)[C:3]#[C:4][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1/[C:14](=[CH:22]/[C:23]1[NH:24][CH:25]=[CH:26][C:27]=1[O:28][CH3:29])/[C:15](=[O:21])[NH:16]2

Participants

7

Reactant 2

HCID 177480913-Pyridinemethanol,alpha-ethynyl-(9CI)HCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2×

Product 1

HCID 9820757HCID 9820757, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Using Method D above, 3-hydroxy-3-(3-pyridinyl)-1-propyne (150 mg, 1.13 mmol) (from Example 24 above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (135 mg, 0.42 mmol) (Starting Material 1) using (Ph3P)2PdCl2 (32 mg) (Aldrich) and CuI (17 mg) (Aldrich) as catalyst in DMF (3 mL) and Et3N (3 mL) as solvent at 70° C. for 17 h, to yield rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(3-pyridinyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 40 mg, 22%).

Sources & evidence

ORD record
ord-7ee28543581b4b7d82e7a951a348a591
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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