Tetrahydrofuran → Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate

HRID 836360Notes

Reaction equation

HRID 836360 reaction equation
[C:14](#[CH:15])[Si:16]([CH3:17])([CH3:18])[CH3:19].[CH2:27]1[O:28][CH2:29][CH2:30][CH2:31]1.[CH3:20][CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH3:26].[Cu:32][I:33].[NH2:1][c:2]1[cH:3][c:4]([Cl:13])[c:5]([C:6](=[O:7])[O:8][CH3:9])[cH:10][c:11]1[I:12].[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>>[NH2:1][c:2]1[cH:3][c:4]([Cl:13])[c:5]([C:6](=[O:7])[O:8][CH3:9])[cH:10][c:11]1[C:15]#[C:14][Si:16]([CH3:17])([CH3:18])[CH3:19]

Participants

8

Reactant 7

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 11776Triphenylphosphine2×HCID 24290Palladium ChlorideHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 66111TrimethylsilylacetyleneHCID 11839203Benzoic acid, 4-amino-2-chloro-5-iodo-, methyl ester

Product 1

HCID 59625799Methyl 4-amino-2-chloro-5-((trimethylsilyl)ethynyl)benzoate

Sources & evidence

ORD record
ord-aff5c3d51a284cc7a58d9cebbe5e9fc2
Source dataset
Test data from https://doi.org/10.1039/C8SC04228D

Reaction notes

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