1,2-Dichloroethane → 8-fluoro-4,5-dihydro-5-methyl-3-[(trimethylsilyl)ethynyl]-6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one

HRID 160811Notes

Reaction equation

HRID 160811 reaction equation
[C:19](#[CH:20])[Si:21]([CH3:22])([CH3:23])[CH3:24].[CH2:25]([NH:26][CH2:27][CH3:28])[CH3:29].[CH2:30]([Cl:31])[CH2:32][Cl:33].[Cu:75][I:76].[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:18]1)[C:7](=[O:17])[N:8]([CH3:16])[CH2:9][c:10]1[n:11]-2[cH:12][n:13][c:14]1[I:15].[Pd:34]([Cl:35])[Cl:36].[c:37]1([P:38]([c:39]2[cH:40][cH:41][cH:42][cH:43][cH:44]2)[c:45]2[cH:46][cH:47][cH:48][cH:49][cH:50]2)[cH:51][cH:52][cH:53][cH:54][cH:55]1.[c:56]1([P:57]([c:58]2[cH:59][cH:60][cH:61][cH:62][cH:63]2)[c:64]2[cH:65][cH:66][cH:67][cH:68][cH:69]2)[cH:70][cH:71][cH:72][cH:73][cH:74]1>>[F:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:18]1)[C:7](=[O:17])[N:8]([CH3:16])[CH2:9][c:10]1[n:11]-2[cH:12][n:13][c:14]1[C:20]#[C:19][Si:21]([CH3:22])([CH3:23])[CH3:24]

Participants

8

Reactant 7

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 198306858-fluoro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515228-fluoro-4,5-dihydro-5-methyl-3-[(trimethylsilyl)ethynyl]-6H-imidazo-[1,5-a][1,4]benzodiazepin-6-one

Sources & evidence

ORD record
ord-ffe60e3f9d154d518172f03fca930bdd
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (9/10)

Reaction notes

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