Acetate → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carbonitrile

HRID 289244Notes

Reaction equation

HRID 289244 reaction equation
[Br:10][c:11]1[c:12]2[cH:13][c:14]([C:20]#[N:21])[nH:15][c:16]2[cH:17][cH:18][cH:19]1.[C:63]([O-:64])(=[O:65])[CH3:66].[C:68]([O-:69])(=[O:70])[CH3:71].[CH3:1][C:2]1([CH3:9])[O:3][BH:4][O:5][C:6]1([CH3:7])[CH3:8].[CH3:22][CH2:23][N:24]([CH2:25][CH3:26])[CH2:27][CH3:28].[CH:29]1([P:30]([CH:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)[c:37]2[cH:38][cH:39][cH:40][cH:41][c:42]2-[c:43]2[cH:44][cH:45][cH:46][cH:47][cH:48]2)[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]1.[Cl:60][CH2:61][Cl:62].[O:54]1[CH2:55][CH2:56][O:57][CH2:58][CH2:59]1.[Pd+2:67]>>[CH3:1][C:2]1([CH3:9])[O:3][B:4]([c:11]2[c:12]3[cH:13][c:14]([C:20]#[N:21])[nH:15][c:16]3[cH:17][cH:18][cH:19]2)[O:5][C:6]1([CH3:7])[CH3:8]

Participants

9

Reactant 8

HCID 175Acetate2×HCID 6344DichloromethaneHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 105144Allyl(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)chloropalladium(II)HCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 591513014-Bromo-1H-indole-2-carbonitrile

Product 1

HCID 591513254-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carbonitrile

Sources & evidence

ORD record
ord-6e4460642ed640d5bc60c33b37bd8608
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (8/10)

Reaction notes

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