Dichloromethane → 7-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

HRID 1553102Notes

Reaction equation

HRID 1553102 reaction equation
[Br:1][c:2]1[n:3][cH:4][n:5]2[c:6]1[CH2:7][N:8]([CH3:18])[C:9](=[O:17])[c:10]1[c:11]-2[cH:12][cH:13][cH:14][c:15]1[Cl:16].[CH2:25]([NH:26][CH2:27][CH3:28])[CH3:29].[CH2:30]([Cl:31])[Cl:32].[CH3:19][C:20]([CH3:21])([C:22]#[CH:23])[OH:24].[Cu:74][I:75].[Pd:33]([Cl:34])[Cl:35].[c:36]1([P:37]([c:38]2[cH:39][cH:40][cH:41][cH:42][cH:43]2)[c:44]2[cH:45][cH:46][cH:47][cH:48][cH:49]2)[cH:50][cH:51][cH:52][cH:53][cH:54]1.[c:55]1([P:56]([c:57]2[cH:58][cH:59][cH:60][cH:61][cH:62]2)[c:63]2[cH:64][cH:65][cH:66][cH:67][cH:68]2)[cH:69][cH:70][cH:71][cH:72][cH:73]1>>[c:2]1([C:23]#[C:22][C:20]([CH3:19])([CH3:21])[OH:24])[n:3][cH:4][n:5]2[c:6]1[CH2:7][N:8]([CH3:18])[C:9](=[O:17])[c:10]1[c:11]-2[cH:12][cH:13][cH:14][c:15]1[Cl:16]

Participants

8

Reactant 7

HCID 6344DichloromethaneHCID 8021DiethylamineHCID 82582-Methyl-3-butyn-2-olHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 198515903-bromo-7-chloro-4,5-dihydro-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198306547-chloro-4,5-dihydro-3-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Sources & evidence

ORD record
ord-26504b54b0da423e82666bd166c964fb
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (1/10)

Reaction notes

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