Tetrahydrofuran → [4-(2-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6ylethynyl)-phenyl]-acetic acid methyl ester

HRID 111430Notes

Reaction equation

HRID 111430 reaction equation
[CH2:30]([N:31]([CH2:32][CH3:33])[CH2:34][CH3:35])[CH3:36].[CH3:18][O:19][C:20]([CH2:21][c:22]1[cH:23][cH:24][c:25]([I:28])[cH:26][cH:27]1)=[O:29].[CH3:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].[CH3:91][CH2:92][O:93][C:94](=[O:95])[CH3:96].[CH:1]1([N:4]2[CH2:5][c:6]3[cH:7][cH:8][c:9]([C:16]#[CH:17])[cH:10][c:11]3[C:12]([CH3:14])([CH3:15])[CH2:13]2)[CH2:2][CH2:3]1.[Cu:48][I:49].[O:37]1[CH2:38][CH2:39][CH2:40][CH2:41]1.[Pd:50]([Cl:51])[Cl:52].[c:53]1([P:54]([c:55]2[cH:56][cH:57][cH:58][cH:59][cH:60]2)[c:61]2[cH:62][cH:63][cH:64][cH:65][cH:66]2)[cH:67][cH:68][cH:69][cH:70][cH:71]1.[c:72]1([P:73]([c:74]2[cH:75][cH:76][cH:77][cH:78][cH:79]2)[c:80]2[cH:81][cH:82][cH:83][cH:84][cH:85]2)[cH:86][cH:87][cH:88][cH:89][cH:90]1>>[CH:1]1([N:4]2[CH2:5][c:6]3[cH:7][cH:8][c:9]([C:16]#[C:17][c:25]4[cH:24][cH:23][c:22]([CH2:21][C:20]([O:19][CH3:18])=[O:29])[cH:27][cH:26]4)[cH:10][c:11]3[C:12]([CH3:14])([CH3:15])[CH2:13]2)[CH2:2][CH2:3]1

Participants

10

Reactant 9

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 10378700Methyl 4-IodophenylacetateHCID 225689952-Cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 69548441[4-(2-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6ylethynyl)-phenyl]-acetic acid methyl ester

Sources & evidence

ORD record
ord-2c734ace8c5d4d1d8541b67bf71e6ce0
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (2/10)

Reaction notes

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